


Kiss at the Crossroads

by Pspquest28



Category: Supernatural
Genre: Brat Dean, Caring Castiel, Cas is suspicious, Crowley and Feelings, Demon Deals, Hand Jobs, Kissing, M/M, Multi, Sam is sick but he'll get better, Secret Demon deal, Sex Slave Dean, Smut, Spanking
Language: English
Status: In-Progress
Published: 2017-01-30
Updated: 2017-04-28
Packaged: 2018-09-20 23:32:25
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 8,326
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9520937
Author URL: https://archiveofourown.org/users/Pspquest28/pseuds/Pspquest28
Summary: Everyone knows when you make a demon deal you'll lose your soul and be damned to Eternity in Hell. Dean knows that, he made a deal before after all. But he has to make one he has no choice. Sam came down with a serious illness a month ago and Dean had carried him to every doctor he could find and there was nothing they could do except stuff him up with pills to help manage.Dean would've asked Cas but at the moment the Angel was still on the hunt for his grace. If he could get it back in time he could heal Sam but who knows when that'll be. So Dean takes matters into his own hands and summons a demon at the Crossroads, little did he know it would be Crowley. One more thing about demon deals is that you have to seal them with a kiss. Well there's no way he would kiss Crowley on any given day, but if he had to in order to seal the deal and heal Sammy hell he would do anything. If only he knew what Crowley had in mind.





	1. Let's Make a Deal.

**Author's Note:**

> I haven't been updating my stories as much as I should have during the past months and I wanted to make up for that with this little piece. I don't know if it's any good, I tried. Let me know if there's mistakes or anything that could use a little touching up. Enjoy!

Here Dean is, standing out in the middle of a crossroads in the middle of a cold, winter night. He's shivering in his boots and can barely breathe in the cold air but he has to do this for Sam.

Yes for Sam, Sam's sick and that's the only reason Dean is out here ready to summon a demon to make a deal to heal his brother. He doesn't even know if the demon would come or not but there's nothing else left to do. 

Sam's barely hanging on as it is. Cas doesn't have any grace to heal, Dean has tried doctors but no luck. Dean even tried praying to God, no answer of course. So now he has only one choice.

Even if he must go back to Hell, he would just for Sammy. He did promise he would go to Hell and back for him. 

He's already buried the little tin can that contains all ingredients necessary for summoning, now he must wait. It must have only been a minute until Dean heard a familiar British accent coming from behind him.

"Hello, Squirrel." Crowley said nonchalantly. Dean swiveled around to come face to face with him. Crowley looked around.

"Where's that Moose of yours?" Crowley questioned.

Dean's jaw clenched along with his fists as he stared down at the gravel beneath his feet. "He's sick." Dean uttered with strain in his voice. He looked up, a hint of a tear in his left eye.

"That's why I'm here. I want to make a deal. Him healed for my soul." Dean said seriously.

Crowley chuckled. "As sweet of a deal that is, you know how this ends and once I have your soul there's no going back. No Cas running to pull you out this time either.." Crowley said. Dean nodded.

"Cas has got no mojo, he can't retrieve me. Just heal Sam." Dean demanded.

"Alright, I'll heal Sam only if he would give up hunting. You think I want that giant chasing my tail after sending you to the Pit?" Crowley smirked. Dean huffed. Convincing Sam to back off would be tough but he'll have to worry with that later, he just needs him healthy again.

"Okay, you got it." Dean grunted.

"Excellent." Crowley said and with that he leaned into Dean, ready to lay a kiss for the deal, but Dean was having none of it. He pulled away quickly.

"What are you doing?" Dean had a shocked expression displayed on his face.

"Sealing the deal, you dingo." Crowley said.

"Yeah I know you close the deal off with a kiss but that isn't necessary, just let me sign something or whatever, I just don't want to kiss you." Dean blurted out.

Crowley frowned. "Come on Winchester, it's a little peck on the lips. It'll barely last a second. Am I not good enough for you?" Crowley teased. "Or are you afraid you'll enjoy it?" Dean blushed, Crowley laughed at him. 

He tried to lean in again to steal a kiss but Dean jumped back out of reach. Crowley smirked at the reaction. It seemed that Dean was a bit defensive with his sexuality, the mere thought of kissing a man sends him running. Crowley assumed this and got an idea.

"Fine. You seem too attached to that masculinity and sexuality, you need those walls broken down. Hmm." Crowley pondered. Dean stared at him in shock, what was he getting at?

Before Dean could even think up something to say, Crowley continued, "How's this? Instead of making Sam give up the hunting life, how about you be my personal slave?" Crowley offered.

"Slave?" Dean said it almost like it was punch to his face.

"Yes, my personal play toy, you can of course still live your regular life, hunt and so forth but when I call for you, you must drop everything and will be summoned to me." Crowley said with a bit of amusement in his voice.

"W-What would you want to do with me?" Dean stuttered. What could Crowley possibly use him for? He was better off killing the hunter.

"Oh I'll just summon you to do some favors… something like a little kissing or maybe a bit of humiliating positions while naked, who knows." Crowley chuckled. Dean's eyes grew wide in horror. He wanted what?! 

"HELL NO!" Dean shouted in his face. He was pissed, how could he even suggest this? At the same time Dean knew in the back of his mind he would end up having to agree, for Sam's sake.

"Alright, you could refuse and let Sam die like a dog." Crowley said.  
"I guess I'll be going then." Just when Crowley is about to teleport off, Dean shouted. "No, wait! I'll... I'll do it." Dean felt defeated, he had no choice. It might not be that bad, maybe Crowley was joking just to get Dean to refuse the deal. 

"Good choice." Crowley clapped and rubbed his hands together. "Now as my pet, the first thing is to let me seal this deal with a kiss. Are you going to refuse me again?" Dean looked mad and he slowly backed away a few steps. Crowley noticed and sighed. 

"Okay if you want it to happen like this." Crowley snapped his fingers and Dean was frozen in place. He was struggling against the invisible grip. Crowley just approached him.

As he closed in, Dean was pleading, "Don't…please." Crowley just laughed evilly. 

"Oh how I love this begging." Crowley said, once he was in reach, he grabbed Dean's waist and pulled the hunter to him as he laid a deep kiss on him. He pushed his tongue against Dean's mouth until his lips gave way and he was exploring his mouth. 

Dean was whimpering against the onslaught but he couldn't protest it since he was powerless. 

Crowley reached around to Dean's back and slid his hand down and grabbed at his ass which elicited a yelp from Dean which was quickly muffled from the kiss.

Crowley pulled away and wiped his mouth. "Not bad. We need to work on your acceptance of kissing it seems." Dean was blushing bright red now and he looked down at his boots. He can't believe that happened and he kind of…enjoyed it. Crowley smiled and grabbed his chin and forced the hunter to meet his eyes. 

"I will see you real soon, Dean. And don't worry when you return back to your Moose, he'll be right as rain." Crowley patted his cheek. He stepped back and snapped his fingers, the invisible force that had held Dean in place vanished.

"Adios." Crowley waved with a smirk and was gone.

Dean was left there standing in the cold once again. Now the deed was done, time to head back to Sam to see if he's finally healed. But Dean couldn't help all the thoughts that were running through his head about Crowley and him being a 'pet' to him. He shuddered at the thoughts.

He snapped out of his own head and trudged back to the Impala, he needed to drive far, far away from here.


	2. First Day as The King's servant

**Summary for the Chapter:**

> Dean's first day.

**Notes for the Chapter:**

> I'm already in love with this fic so I'm posting this chapter quickly. I hope whoever is reading is loving it as much as I am.

Dean was nearing the Bunker and he was driving at an incredible speed, if Sam was healed he wanted to see him for himself and hug him tightly.

Dean was to the Bunker in less a minute, he slammed the Impala door, silently whispered a small apology to his Baby for the harsh slam and ran up to the door to unlock it.

He got in, secured the door and ran off to Sam's room quickly. He didn't have to get far because Sam wasn't even in his room. He caught him in the library, he was sitting down on his laptop while sipping some coffee. He seemed fine, like he wasn't fighting a fatal disease a few hours ago. He saw Dean nearby and greeted him.

"Hey, Dean. I know you must be surprised." Sam chuckled. Dean was more than surprised.

"Dude, you look amazing, like brand new." Dean had a big grin. 

"I don't know what to say. A few hours ago, I was laying on the bathroom floor, spilling my guts out and now I couldn't feel better." Sam beamed. Dean was uneasy the whole ride up to the Bunker, he wasn't sure about how this deal would backfire on him and what the risks really were but now he realized that it was all worth it now to see this smile on his little brother's face.

Dean rushed over and hugged him. He didn't care if it looked chick flicky, Sam was okay and he was damn happy about it. 

He wouldn't dare tell Sam about the deal, he's still stumped on how to explain to Sam when he has to disappear to attend to Crowley. He'll have to cross that bridge when he gets to it.

"We got to let Cas know you're okay now so he doesn't have to run around crazy like a chicken with its head cut off looking for his Grace." Dean joked. Sam chuckled at his comment.

"He already knows, he had stop by earlier to see how I was fending and he was relieved to see I was alright now." Dean was relieved as well when he heard that. Well at least that's taken care of.

"Now, since we don't have to worry about your health, how about we take a break from hunting and life for a bit and relax?" Dean offered. Sam nodded.

"Sounds great. How about a movie? Terminator is on Netflix now." Sam said. Dean agreed and headed off to the kitchen to make popcorn.

They relaxed in the living area watching the Terminator movie and after it was over they decided to make it a double feature with The Nightmare on Elm Street.

It was late so both brothers decided to head in. Sam wobbled off, sleep already starting to capture him. Dean cleaned up and headed to his room as well, when he got to his bed he had collapsed into it. Happy to be engulfed in the memory foam.

\---------------------------------------------

Dean woke to the sound of his phone buzzing on his nightstand. Lazily, he grabbed for it and answered it without looking to see who it was.

"Hello?" Dean's voice heavy with sleep.

"Squirrel." Crowley greeted. "You sound exhausted." 

Dean sat up and huffed. "Yeah, yeah. What do you want?" Dean grunted.

"Well, I was just thinking that today would be a great day to break in my new toy." Crowley said as Dean groaned into the phone.

"Yes, Squirrel. Now I'll give you an hour to get ready. Call me when you're done and I will summon you here." With that said, Crowley hung up.

Dean sighed. Already he had to fulfill his side of the bargain. He looked at the time. It was barely 11 am yet. He got up and headed for the bathroom.

He spent a long time in the shower contemplating all of this. Crowley, the deal, Sam's recovery. He was tired and irritated about this stupid deal but he had to do it, afraid that Crowley would undo Sam's healing. 

He hopped up out of the shower, got dressed and went to the kitchen to whip up a quick breakfast, that being a half eaten piece of pie and a bottle of beer. It wasn't the best way to start the day but he didn't care.

He peeked his head in to the library and saw Sam. "Hey, I'm heading out to the grocery store later today." Dean lied, he needed an excuse so Sam wouldn't be suspicious of where he was going.

"Okay, make sure you pick up a few of those protein bars." Sam didn't even look away from his computer. Dean shrugged and left the Bunker.

Once he was outside he rang Crowley's phone and before he knew it he was face to face with Crowley once again.

"I just assumed you're calling me to summon you so I just went ahead and did it." Crowley said as he stared Dean down.

Dean cancelled the call and pocketed his phone, now he was left staring at him sitting at his throne.

"Did you have a breakfast?" Dean gave him a confused look.

"What? I'm just making sure you've eaten. You'll need your energy." Dean gulped at the last statement.

"I had a little something." Dean managed as he looked at the floor.  
Crowley got up, "Well, that must mean you need to eat. Let's go, follow me. And you need to stop staring at the floor, my eyes are up here." Crowley lifted his chin again as he walked past.

They headed to the dining room where there was a long dining table made of what look like mahogany, it was a big enough for about 50 people to sit at but only one plate was set out with silverware and a glass of water. It was placed at the head of the table where Crowley was heading. He sat down and gestured to the cushion that was placed on the floor next to the chair. "Kneel." He said. 

Dean stared at the cushion and back at Crowley like a silent "Are you kidding me?" Crowley frowned.

"Kneel now, brat." Crowley pointed to the cushion yet again. Dean made a face at the name Crowley called him but he kneeled anyways.

"Good boy." Crowley patted his head which made him mad and turned his gaze away from him. Crowley chuckled.

"Now I have here a nice breakfast platter. Prepared just for you. I assumed that you wouldn't have time to eat since I gave an hour to get ready." Dean looked over at the plate. It was packed with eggs, bacon, pancakes with maple syrup drizzled lightly. Dean's mouth watered at the sight.

Crowley picked up a forkful and pushed it into Dean's reach. Dean turned his head away from it, the food looked tantalizing but it could be drugged and Dean wasn't about to let that happen to him.

Crowley heard the thought. "It's not poisoned. Now eat." Dean sighed, he knew Crowley would be relentless so he reached for the fork only to have it pulled out of his reach. "Ah ah ah, I feed you. Pets do not feed themselves." Dean pouted at that.

"Don't be angry, brat." Dean hated that name. Fine, if he wanted a brat, he'll get one. Dean opened his mouth for the food, and once Crowley fed him it, he chewed. Crowley uttered a 'Good boy' but then Dean spit the mouthful of food back and laughed at Crowley's surprise.

"You think that's funny, huh?" Crowley's face crack into a wide grin. "Alright. Feed yourself, when you're done meet me in my throne room." Crowley got up and went ahead to his room bit before he walked out he said, "Don't keep me waiting." 

Dean gulped as he watched he leave. He got into the seat quickly and started shoveling his breakfast into his mouth, he knew this'll probably be the last time Crowley would let him feed himself so he took advantage. He also knew he's in big trouble.

\----------------------

Dean hesitantly entered the room, Crowley sitting in his usual spot which was his throne, eyed him.

He crooked a finger at Dean. "Come here, Squirrel."

Dean was scared, he can admit. All the monsters he's faced in his life but this moment seem to keep him on edge.

"What are you going to do?" Dean questioned.

"You'll know when you come here. Now come here. I won't say it again." Crowley yelled. Dean hurried over and now he was standing in front of the mad demon.

"I know you're mad but you got to give me a break." Dean pleaded. Crowley held up a finger, a sign of silence for Dean.

"You know you were naughty. Now I have to correct you." Dean inwardly giggled at the word 'naughty' but he was then quickly pulled by the wrist and he was placed over Crowley's left knee. His eyes grew wide in realization.

"No, wait you can't be serious!" Dean yelled, he tried his best to struggle but he was held down firmly.

Crowley smiled and began spanking Dean's backside. "It seems you're well over due a lesson, I've been dying to do this for a long time. All you Winchesters need is a good old fashioned spanking." Crowley punctuated his words with hard smacks to Dean's sit spots.

Crowley was satisfied when he heard the yells and grunts coming from the hunter. He let him up, grinning at Dean rubbing his backside. 

"Next time, it'll be on the bare and if you're learned anything from this that is there should be no next time. Am I clear?" Dean nodded. 

"Good. Now come sit in my lap, we need to discuss rules and what I expect of you." Crowley patted his lap, Dean shook his head and backed up a step. There's no way he's sitting in his lap! 

Crowley sighed, "Not this time Squirrel." Crowley flicked his wrist and Dean was dragged by an invisible force to Crowley. He was then pulled into his lap until he was straddling him. Dean blushed at being in such a position, he was practically on top of Crowley's crotch.

"Now, rules first. Whenever I call you and tell you that I will summon you, you will prepare yourself for when I summon. I know when you're in the Bunker, I cannot use my power to summon you since there are wards so you need to be outside those wards before you give me the go ahead." Dean nodded.

"And if you think just because the Bunker is impenetrable by me, you can hide out there to try and avoid me you're wrong. You'll have to come out of there at some point and when I get my hands on you, you won't like it." Dean visibly gulped. He didn't say anything though.

"You're awfully quiet, I would have expected a bit of mouth from you by now." Crowley ran his finger across Dean's lips. "Hmm, this mouth was meant for more then mouthing off though. Maybe I should make use of it later?" Dean eyes bugged out, no…he couldn't mean… Crowley chuckled at the reaction.

"Yes Squirrel. I will be using you in certain ways. Some days I might ask you to suck my cock or just keep it warm while I'm working. Or I might fuck you for my release, your job is just to please me." Crowley laughed sadistically as Dean whimpered. He didn't want to those things! Blowjobs and getting fucked?! No way!

Dean shook his head. "Dean, you will do it. Do you want me to undo Sam's healing?" Dean got scared. "No! Please don't. I'll do whatever." Dean pleaded.

"Good. Now, one more thing, I will try numerous different things on you to see what kinks or fetishes you enjoy. I'd love to hear you as you moan. But we will cover all of that soon so that's it for now." Crowley winked. "Any questions?" Dean thought for a moment then he nodded.

"Yeah, if there's rules there must be rewards and punishments right?" 

"Yes indeed. I'll reward you from time to time when you're good like giving you breaks from serving me and with punishments I'll be spanking you, timeouts, orgasm denial and much more." Dean gaped at the punishments. He was in trouble.

"Don't worry, pet. You won't be punished if you behave." Crowley patted his head.

"Now, with all that said. Let's have some fun." Crowley said as he reached for the button of Dean's jeans. Dean saw where his hand went and tried to pull away. Crowley just unzipped his pants and pulled out his cock and Dean shuddered at the contact.

"Nooo…" Dean managed. Crowley laughed, he summoned up some lube and drizzled some in his palm and went to work. He grabbed Dean's cock and gave it a few slow strokes and twisted up and swirled his thumb over Dean's head. Dean tried his best to hold back his whimpers and moans. Crowley noticed and sped up his ministrations to elicit the sounds out of him. Dean was bucking against Crowley unaware. 

"Look at you Dean. So good for me. Can't wait to have you stretched around my cock." Dean whined at the comment and shook his head fiercely. The day he let a demon fuck him is the day he shoots himself, but whose he kidding? He's sitting in a demon's lap, getting jerked off by said demon.

Crowley sped up the movements and before Dean knew it he was coming everywhere, his jeans were smeared as well as Crowley's suit pants and Dean screaming at the top of his lungs with pleasure. Crowley just smiled triumphantly, he must be pleased to reduce a Winchester to moans and whimpers.

Crowley reached down and scooped some come onto his index and middle finger and held it out to Dean. "Lick them clean, pet." He pushed the fingers closer to his lips. Dean turned his head immediately, he wouldn't dare eat his own come. Crowley sighed.

"You either let me put these fingers in your mouth and you suck them clean or I take every last bit of this come splattered here and put it up your ass." Crowley threatened and Dean went stiff at this. He stared at Crowley's fingers which glistened with his own release. 

Dean thought about it for a minute, come in his mouth or come in his ass. He decided that he'll just brave it and suck the fingers, hopefully he won't vomit.

Dean took in a deep breath and let it out. He went forward and too the fingers in his mouth. It tasted weird he can admit, tasted something similar to how women tasted down there but not as sweet as theirs. He continued to suck and breathed through his nose. Crowley just watched on in amazement and victory. 

"Good boy. Make them nice and clean. Boy those lips were made for sucking." Crowley grinned and pulled his fingers from the hunter's mouth. "Now swallow." Dean didn't want to. He was about to spit it out when Crowley cut in.

"Don't you dare, Squirrel." He flicked his wrist and made Dean swallow it involuntarily. Dean was surprised and embarrassed at the same time. He shook out his tongue, hoping to get the taste off it.

"Next time I expect you to do something, you do it without thought. I'm finished with you for the day." Crowley fixed Dean's clothes again and snapped his fingers, sending him back to the outside of the Bunker again.

Dean sighed, at least that's over for now. He entered the Bunker.

Sam greeted him, "Hey, where's the groceries?" He questioned. Oh Damn it."Oh crap." Dean uttered aloud.

Sam laughed. "You never went to get groceries did you?" Dean shrugged with a face of defeat.

"You got me, I was uh… with a woman." Dean lied.

"That's explains why you look so wrecked." Sam was amused. He headed back into library whistling. Dean just heard back to his bedroom, he was exhausted.

————

Dean slumped onto his mattress. Oh man was he wiped. That was the most intense orgasm he's had in…well ever. He can't believe he let Crowley see him like that. Dean slung an arm over his eyes.

Dean then heard a swoosh noise and sat up to find Castiel staring at him. "Dean, where were you today?" Dean looked at him surprised.

"First off, how did you get your Grace back?" Dean asked. He was happy to see the Angel back with his mojo.

"Oh yes, I have recovered it from Metatron, sadly I must say I had to kill him for it but what's done is done. Now where were you?" Cas demanded once again.

"Well, uh I was… does it matter?" Dean blurted. "What I do is my own business." Dean got a bit defensive.

Cas narrowed his eyes. "Fine, I won't ask you anymore." Cas left the room in a flash.

He left Dean confused. "Okay…" Dean muttered.

**Notes for the Chapter:**

> That was a bit difficult for me to write. I know you're wondering when the DeanXCas come in but it will soon by either next chapter or the fourth one. So stay tuned!!


	3. Enter...Castiel

**Notes for the Chapter:**

> It took me so long to get his out and i feel like this wasn't as good as i wanted but I tried lol. Let me know how it was! P.S. not beta read.

Dean’s alarm went off for 6am, this was his second and last day of his and Sam’s hiatus from hunting. He got up early just in case Crowley rang him for another summoning. He was already tired of the little demon, and he can already see that this deal will come back to bite him on the ass.  
He got showered and dressed quickly and actually had a decent breakfast of French toast and coffee, minus the beer. He practically inhaled his food and chugged the coffee and set off to immerse himself in some TV.

At about 1p.m, he was lounging around and bingeing his all-time favorite show Dr. Sexy, M.D. when his phone vibrated violently on the coffee table. I bet he could take a wild guess and know whose calling. He grabbed it up and of course, the not-quite the devil himself.  
“Hello, Squirrel. Mind keeping me company today? I even have a little gift for you.” Crowley said, a little too delighted. The way the word _gift_ rolled off his tongue put Dean on edge.  
“Hm, sounds like that gift of yours will be something I won’t enjoy.” Dean said through the phone.  
“Oh Squirrel, you know me so well, but don’t worry I’m sure you’ll enjoy it too. I assume you’re dressed and ready for the day, are you at the Bunker?” Crowley chimed.  
Dean was ready to lie and say he was busy on a hunt out somewhere but he knew Crowley would probably use his powers to pinpoint his location, so he went ahead and spilt the truth.

“Yeah, I’m there. Summon me in a minute, I’ll go outside.” Dean said as he walked towards the stairs to climb up.  
“That’s a good squirrel and by the way, you are correct.” Dean frowned.  
“About what?”  
“I would have pinpointed your location to confirm where you were. I’m glad you decided against lying. It wouldn’t have ended well if you did.” Slight amusement trickled into Crowley’s voice.

Dean frowned deepened. “And what would you possibly do?” Dean challenged.

Crowley chuckled. “Well, let’s just say that after I’m through, you wouldn’t be able to sit comfortably for a while.” Dean paled at his comment.  
“Y-You can’t be serious. You wouldn’t dare!” Dean yelled.  
“Oh? Try me and see what happens. Now I advise you to get your little whiskey-drinking, pie stuffing, denim clad backside out of that Bunker so I can summon you.” With that said, Crowley hung up, leaving Dean gaping at his phone screen.

The nerve of that prick, Dean’s had it with the guy. It’s only been a few days but he’s fed up and tired of Crowley’s orders. So Dean decided to do something he knew he’ll regret later. He took off his boots, left on the socks. Went to the kitchen and grabbed a bottle of beer and came to sit in the living room, resuming his show.  
If that dick of a demon wanted a challenge, he’ll get one alright. Dean took a big gulp from his beer.

Only ten minutes had passed and Dean wondered if Crowley wasn’t interested anymore. Just as he thought that, his phone buzzed on the coffee table. Bingo.  
Dean picked it up and glanced at the screen, yep it’s the littlest pain in the ass, Crowley. Of course he just put the phone back on the table and immersed himself in his show once again.  
The phone kept buzzing repeatedly but Dean ignored every single call, smirking to himself.  
Text buzz. Hm. Dean decided to check. Let’s see what Crowley has to say now.  
Dean checked his messages and found what looks to be an essay of a message, he has to blink a few times to make sure he’s seeing right.

The message states:  
_Squirrel, I’ve been trying to summon you for the past 5 minutes and it seems something is wrong, I’m assuming you never left the Bunker and that saddens me deeply that I will have to take you to task. I will be there shortly and I hope that once I’m through, you will see the error of your ways and won’t try this again. And don’t say I never told you there were consequences to your actions._

As Dean read this, his skin paled and sweat began to form on his brow. Crowley doesn’t mean that, no way he could! Time to go hide then.  
Dean shot up and turned off the television and scurried to his room, bumping into Sam in the hallway as he went and knocking Sam’s books out of his hands.  
“Hey Dean, what’s the rush?” Sam questioned, Dean tensed.  
“Uh…uhm, it’s Crowley, he’s been nagging me today, that’s all.” Dean lied, it was the best he had at the moment. Sam narrowed his eyes at his brother.  
“What does Crowley want? There’s no reason for him to bug us for anything.” Sam huffed. Dean just shrugged at his brother, trying his best not to just flee to his room. He has to get going, Crowley will be banging on that door any minute!

Just as he predicted, there was a sharp bang which echoed through the Bunker, Dean gulped. Sam sighed. “Well, I have a pretty good idea who that is, let me see what the guy wants.” He said as he turned on his heel towards the banging noise. Dean hurried his way to his room at this point, slamming the door and sitting on the floor with his back against it.  
Damnit, he should have gone when Crowley wanted him, now the demon is going to make him sorry. Why the hell is he so stupid sometimes! All he had to do was get summoned by the prick and do what he’s supposed to, even if it might be humiliating! He must do it for Sam, he doesn’t want his baby brother to turn ill again because he refused to hold up his end of the bargain with Crowley. Maybe he can plead mercy on himself and his bro, Crowley might still punish him though and oh God he doesn’t want another spanking. He could have barely taken the last one and that was only a few swats, and he doubted Crowley was even using all his strength!

Dean realized that it was real quiet now. No sound from upstairs either, was it Crowley that even came to the door, oh no, did he do something to Sam?! What kind of brother is he that he didn’t think before letting Sam answer the door?  
Dean stood up fast and grabbed for the doorknob, but stopped on half turn. If he opens this door what will he face exactly? A pissed off demon seething at the mouth ready to deal with Dean or Sam on the floor of the Bunker in a coughing fit and pale as paper like he was a while back? He must know, he can’t stay in here another minute and not know what’s going on.  
He gathered up his courage and prepared for what will be presented before him. He turned the knob fully and pushed open the door warily, peeking out before opening the door completely. No sign of Sam or Crowley anywhere in the halls, the coast is clear.

He carefully tiptoed out of his doorway and shut the door quietly as to not make a sound. Dean doesn’t even know why he’s so scared of Crowley anyway. So what if he’s pissed at the hunter for not being in the mood for his antics today, he just wants to relax and enjoy his day off. Now he has to go face his consequences for not obeying Crowley’s direct order.  
Dean creeped up to the upper floor with ease and came around the corner of the library and was greeted with quite a scene.  
Crowley sitting in one of the libraries’ chairs at the far end sipping his favorite drink, 30-year-old Craig from a tumbler. Sam nowhere in sight and Dean is worried like hell.  
Crowley spotted Dean right away and he had a big frown spread across his face. Yeah, he’s not happy. Crowley got up from the chair ominously and Dean got a chill which rose up his spine as Crowley stepped closer to him. Dean eyes bugged out.

“W-where’s Sam?” Dean stuttered out as he watched Crowley cautiously.  
Crowley shook his head. “Oh Squirrel, don’t worry I’ve done nothing to Jumbo. He’s out on his errands. I settled that I was here to speak with you and the business is only between us. Sam didn’t mind much since he believes you can take me if necessary. Now here we are, and it’s time to talk about your disobedience.” Crowley said nonchalantly.  
Crowley was now face to face with Dean, or should we say face to chest. Dean was half tempted to make a snarky comment on Crowley’s small frame, but decided against in fear of making the demon even more pissed. Crowley reached out and touched Dean’s left wrist and asked, “Okay where shall we do this?” Dean had a confused expression written on his face.  
“What are you talking about?” Crowley smiled at the question.

“Your spanking. Where shall we perform it, I assume you want to do this somewhere private so your bedroom would be ideal?” Dean stared at the demon in horror, Crowley was saying this like he was talking about the weather.

Dean had a billion thoughts running through his mind. Will Crowley really go through with what he’s proposing? He can’t really be serious yet Crowley had already swatted him before but that was just few hits. Dean doesn’t think he could take a full spanking from him and he was having second thoughts taking this like a man. He rather run like a little mouse and hide in the corner.  
Dean quivered and he was ready to turn heel and beat it when he was halted in place yet again by Crowley’s invisible force.  
“Now, Squirrel. I don’t think you want to test me. You’ve already angered me as it is, now you must face the consequence.” With that said, Crowley started to walk in the direction of Dean’s room, dragging Dean along with him by the invisible grip. Dean had struggled but it was futile, he knew he couldn’t stand a chance against Crowley’s power, so slumped and let Crowley pull him along.

Dean was standing, facing Crowley who was sat on his bed with his arm crossed. Dean gulped. He had to do something.  
“Okay Crowley, let me explai- mm” Crowley had cut off Dean’s words by a flick of his wrist and Dean’s mouth was shut.

“I don’t need an explanation for your behavior, Dean.” Crowley growled. “Besides, I doubt there’s anything you can come up with that can change my mind on punishing you.” Crowley said with harshness rippling through his voice. Crowley grabbed Dean easily and pulled him over his lap. Dean wanted to scream at him and tell him to release him, but his mouth was still snapped shut.  
Crowley snapped his fingers and Dean could move his mouth again. The first thing that was shot out was “Hey! Let me up you bastard!”. Dean yelled and squirmed over the demon’s knee. This was down right humiliating, he may have allowed Crowley to spank him last time because he was in shock. But there was no way in Hell he was letting this happen again!  
Crowley ignored Dean’s pitiful attempts at escaping and just placed his left hand at the small of the hunter’s back. He slowly raised his right hand in the air, that’s when Dean’s whole body stiffened and Crowley swore he heard a hitched breath. Crowley brought down his hand with a great deal of force and the sound of hand meeting denim had reverberated through the room.  
Crowley kept up the pace as Dean yelped and squirmed through the assault.

“You should be grateful that I left your jeans and underwear up. This could have been much worse.” Crowley commented.  
Crowley repeatedly hit him and Dean had to hold back as many yelps and whimpers as he possibly could. He felt tears beginning to prick at his eyes and he knew he couldn’t let Crowley win this one. He wasn’t going to break, he just had to hold off till the demon got tired.

Crowley was reading his thoughts and knew he had to break down those stubborn walls Dean always hold up. He would spank him forever if that is what it takes to get the Winchester to listen. He continued to lay smack after smack onto Dean’s backside, now he wondered what the shade must be. He doesn’t want to hurt the guy…no why should it matter if he hurt him or not? Crowley shouldn’t care, he’s the King of Hell and master of torture. He lives for the pain and misery of others, so why must he feel guilty for smacking Dean so hard.  
Crowley decided to loosen Dean’s jeans and pull them down along with his boxers, catching the sight of Dean’s dark pink backside. ‘It stills needs a bit more warming.’ Crowley thought.  
Dean’s eyes widen. “Hey, hey! Why are you…no! Pull them back up, right friggin’ now!” Dean shouted.

Crowley smacked him again to silence him. “I don’t need to hear another word out that mouth of yours!” Crowley yelled and started his onslaught of smacks again. Dean just laid there, defeated and took the smacks as best as he could but it was horrible!  
A particular slap caught Dean on the top of his thigh and he yelped harshly, on the edge of it being too much and Dean was on the brink of tears. He couldn’t break, he could not give Crowley the satisfaction.

Next thing Dean knew, he heard wings whooshing through the Bunker. Dean’s blood ran cold and he went stiff, the smacks also had ceased. Oh God.  
“Dean? Crowley? What is happening here?” Cas asked, he took in the sight of his friend sprawled over Crowley’s lap with said demon with his hand raised in midair.  
Dean was shocked he didn’t know what to say and he refused to even look in the direction of the Angel, besides he was blushing like a schoolgirl at this point.  
“I heard Dean’s soul cry out in distress and it resonated thorough my Grace so I came as soon as possible, but I’m confused to why Dean is in this position as if to be stricken like a child.” Cas said with ease and not even batting an eye. Crowley was silent and didn’t bother to answer the Angel.

Cas had look over to Dean, the hunter could feel that stare boring into the back of his head. He turned enough to peek over his shoulder and saw the Angel staring directly at him. He wanted to explain but the words weren’t getting out so he was just silent. All he did was cry silently, a few tears trickling down his face.  
He felt a tissue being blotted against his eyes and nose and looked up to realize it was Crowley wiping his tears and Cas was looking on and smiling. What the heck is going on?  
After Crowley had dried Dean’s face, Cas spoke, “Now Dean since neither you or Crowley want to tell me why he is punishing you, I will find out myself.” Cas approached Dean, the hunter tried to get away but forgot the demon was still holding him by his waist firmly. Cas placed two fingers on Dean’s forehead, the hunter felt a flush of something run through him then as quick as that, Cas removed his fingers.

“I see, you made a deal with Crowley to heal Sam. That explains why he’s better.” Cas figured. “But you have to serve Crowley, so that seems to be the catch here.” Cas turned to look at Crowley. “What’s your motive here?”, Cas questioned.

Crowley just stared at the Angel, but he eventually found his voice and spoke up. “This deal really was to use Dean as I see fit, but my plans changed and I was now considering training Dean to his full potential.” Dean rolled his eyes at Crowley’s statement. Training? Yeah right, more like torture.  
Crowley caught the sight of Dean rolling his eyes over his lap and gave him a quick smack on his left thigh. “Quiet, Squirrel. Unless you want me to pepper your backside again.” The smack drew a surprised yelp from the man and he silence himself after that. Dean shyly looked over at Cas and was shocked to see the Angel smirking at him.  
“Well it seems you have Dean under control. I never thought I’d see the day he’d listen to anyone.” Cas said amusedly. Crowley chuckled.

“Well, he knows what I expect from him and if he doesn’t live up to those standards and boundaries I make, he would be punish severely. I run a tight ship in Hell and I’ve had a lot of practice with unruly subjects. Dean here is no challenge for me.” Crowley reached his hand out and ruffled Dean’s hair playfully. Dean was beyond pissed at this point, he wanted to crack a good punch across Crowley’s jaw for this.

Crowley looked at Cas. “But you know I could always use a partner in disciplining Squirrel here.” Dean’s eyes widened and he began to sweat. Oh no no no! Dean then began to struggle a bit to try and get up off Crowley’s lap, but with the iron grip Crowley held on his waist there was no way he was going anywhere.  
“I’m not opposed to this arrangement that you and Dean have in fact I encourage it, but if you want me to be a partner in crime we have to stand on equal ground with decisions regarding Dean.” Cas said cooly. Dean’s mouth hung open. What the fuck?! Cas was actually considering this?? Dean could stomach Crowley doing this but Cas of all people joining in? Dean sighed and squished his face into the bedsheets, this was gonna be a long ride.

“That can be managed, between you and I we can write up rules to help maintain Dean. It seems he doesn’t always care for himself as he should. Eating unhealthy and drinking excessively is his major problem here too so we’ll have to work on that.” Crowley said as he stroked Dean’s back. Dean was confused, why the hell was Crowley even interested in him eating right or whatever. He’s a grown man an if he wanted to eat greasy foods or drink loads of beers well it’s his god damn right!  
Cas nodded at all of Crowley’s words. “I agree, what also needs to be address his Dean’s attitude and constant recklessness. The amount of times Dean has cause himself harm on hunts has exceeded greatly and I worry on a regular basis for him.” 

Crowley and Cas both continued to talk for a while but at this point Dean just drowned out their conversation. After a while, Dean felt himself being lifted from Crowley’s lap and placed in a sitting position on his lap. Cas was crouching near them and stroked Dean’s back gently, they also made sure Dean’s ass didn’t scrape against anything to agitate the soreness. Dean had his eyes closed the whole time. He didn’t want Crowley or Cas staring him in the eye right now, this situation was already embarrassing enough.  
Dean felt something like glass being placed to his lips and on instinct he opened his eyes to see what it was. It was a glass of water which Cas currently held to his mouth. “Drink up, Dean. You’re probably dehydrated at this point.” Cas said.

Dean honestly didn’t feel for a drink of water, he was parched though and took a sip from the glass. “Good, that’s it.” Crowley encouraged.  
Dean chugged the whole glass down in minutes, the cool water worked through his system and gave him a more calm and refreshed feeling. Dean was so dazed and lost in relaxing he hadn’t heard Crowley speaking till he felt a hand on his cheek, lightly tapping it.

“Squirrel listen please. Cas and I from now on will be making sure you are taken care of and well behaved. I, of course will still be giving you some sexual training here and there and I don’t know if Cas will be doing the same thing, I guess you and him will be discussing that topic.” Dean froze up a bit there, he never thought about Cas and him ever being sexually involved, but he wouldn’t admit to considering it at a point. It was just odd now that Cas is like family to him now.

Dean couldn’t argue right now he was really tired, he just nodded. Cas saw how exhausted Dean looked. “Okay, looks like you need rest Dean. Come along.” Cas took Dean out of Crowley’s arms with ease and carried him over and laid him on his bed. Crowley tucked him in and stroked his hair. Dean was so dazed, he couldn’t believe Cas and Crowley were doing this. It might just be a dream and he’ll wake up and find himself alone in his room like always. 

“Oh and Squirrel. Remember that gift I was supposed to give you when you were to be summoned?” Dean slightly nodded.  
“Well, I leave it on the bed for you. I will be back in a few hours and we could discuss what I want of you. Have a good rest now.” With that said Crowley was gone. Cas was left there now. “Rest now, Dean. I sense a lot of your energy has diminished and you need to replenish it.” Cas patted Dean’s head and walked out the room.  
Dean was finally alone, and he honestly didn’t want to sleep just from the mere fact that Cas and Crowley want him too. He wanted to be defiant but the bed felt too good to leave. So he just let his body sink into the memory foam with a sigh. After a few moments, sleep engulfed Dean.  
====================================================================  
Dean had awoken after two hours of rest. He stretched and rolled his shoulders and wiggled his toes, boy did he sleep like a rock. He was beginning to wonder if that situation with Cas and Crowley was a dream or not, but then he felt the sting of his ass against the bed and yelped as he jumped up. Yeah, definitely not a dream.  
He saw a white box which sat at the foot of his bed and reached for it, his curiosity peaked. Dean looked over the box, and he didn’t realize that Crowley was even watching him till he heard a throat being cleared.

He looked up with alarm but it was short lived when he laid eyes upon the demon. “Go on open it.” Was all Crowley uttered. Dean was hesitant at first but he slowly began to inch the lid off the top. When he looked inside, he blushed a deep red and slammed the lid back on.  
“No way! Ain’t happening!” Dean declared. He drew the line here, there’s no way he’s wearing it!  
Crowley chuckled. “Okay, let’s go over what I want from you. You can choose to ignore me if you want but punishment will come if you decide to do so.” Dean grumbled at Crowley’s words and crossed his arms like a petulant child.

Crowley opened the box and removed the article of clothing which happened to be a pair of red silk panties with a cute dark red bow on the front crotch.  
“I know you will start looking for cases and get back into the hunting game with Sam. Now, both Cas and I worry that you’ll get reckless like usual, you always barge in with guns blazing and just start tearing the place apart.” Dean can admit that the guy was right. He shrugged but wanted to know what the panties had to do with it.  
“Now I want you to wear this little number when you hunt with Sam again, this way you’ll be a little bit more carefully with running around and being reckless. I’m sure you don’t want your shirt flying up and flashing your brother your nice undies, am I right?” Crowley questioned.

Dean nodded with his blush deepening. He was going to protest but realized he could just say he’ll wear it but not go ahead and do it. Just play along with him but don’t make it too obvious.  
“Yeah fine. I’ll wear the damn things but only during the hunt, the minute I get the chance to remove them, I will. Crowley grinned.  
“Good! As long as you keep your word. Don’t want to have another sore bottom I bet.” Crowley teased and threw the underwear at him.  
“But just in case you do feel the temptation of not going through with it, Cas will be accompanying you on the hunt and will regularly check that you’re still wearing them.” Dean groaned. Damnit his only chance of getting away with this just went out the fucking window.

“I hope this will help teach you how to be more careful on hunts. Now, happy hunting. By the way you look so cute blushing. I think that blush goes well with those panties, I should make them a part of your everyday wardrobe.” Crowley said as he grinned and walked out, leaving Dean with his mouth gaping like a fish, panties strewn across his lap.

**Notes for the Chapter:**

> Was it decent? Let me know!


End file.
